Oil additive



Patented Dec. 5, 1944 OIL ADDITIVE Alfred L. Bayes, Kenmore, N. Y., assignor to Carbide and Carbon Chemicals Corporation, a corporation of New York No Drawing. Application June 17, 1943, Serial No. 491,227

Claims.

The interaction which takes place is believed to proceed in accordance with the following formula:

CHr-CH:

4o NH+ s on CHz-Cz out-on: orig-cm Caz-cu? o n-s-n 'o+20 NILHCI out-0H, our-CH2 om-cm As an example of the reaction conditions suitable for preparing this new compound, four mols (348 gms.) of morpholine was dissolved in 500 gms. of benzene, and the solution placed in a three-neck flask fitted with a stirrer, dropping funnel, and condenser. An ice bath was placed around the flask and thetliguid cooled to 0 C.

One mol (103 gms.) of sulfur dichloride, diluted with an equal weight of benzene was then added to the cooled morpholine solution at such a rate that the temperature was maintained between 0 C. and C, After all of the sulfur dichloride had been added the mixture was allowed to warm to room temperature slowly. and was allowed to stand for several hours. Finally, the mixture was refluxed for two hours over a Water bath, and after cooling, the precipitated morpholine hydrochloride was filtered off. The filtrate was washed with water to remove all water-soluble chlorides, and then dried over sodium sulfate. After removing the solvent under diminished pressure, the remaining solid product was further purified by recrystallizing from ethy alcohol.

Analysis of the final pure product showed a sulfur content of 15.6%, and indicated a dimorpholine monosulfide derivative of the structure as above shown. The compound is a white crystalline material having a melting point of 112 C. It is soluble in common organic solvents such as benzene, alcohol and ether, and is essentially insoluble in water.

As a further embodiment of this invention I have found that dimorpholine monosulfide has oil solubility, and that when incorporated with oil it exerts an anti-oxidant function. The compound has value, therefore, as an inhibitor additive for lubricating oils, gasoline and other oil products. As an additive for internal combustion engine lubricants, dimorpholine monosulfide is both an anti-oxidant and a corrosion preventive, and, unlike many sulfur compounds which have been proposed for analogous uses. it does not promote corrosive attack on copper and copper alloy bearings.

In both laboratory and full scale engine tests the ability of dimorpholine monosulfide to retard deterioration of conventional lubricating oils has been well proven. For example, in additive amounts of 0.5% by weight to a Pennsylvania solvent refined oil, S. A. E. 20, this inhibitor has reduced by well over half the amount of oxygen absorbed by the oil in a standard laboratory oxidation ,test, while at the same'time substantially retarding deteriorating changes in oil properties, such as those measured by neutralization number and amount of naphtha insoluble. Correlating results have also been obtained in 36 hour Chevrolet engine tests, where 0.5% climorpholine monosulfide in a conventional Mid Continent solvent-refined oil has greatly retarded bearing corrosion, and substantially improved oil stability.

The most effective concentrations of this new additive will vary with different oils, and with different lubrication conditions, but for most pur poses amounts from about 0.10% to 2.0% will be found satisfactory. In extreme pressure lubrication higher concentrations, of 5.0% or more, may be desirable, and use of the additive in this capacity is contemplated in the broader scope of the invention. Likewise the invention does not exclude the presence of other additives along with dimorpholine monosulfide, where materials such as detergents, oiliness agents, or other property-modifying compositions may serve a further function in specific lubricant uses.

I claim:

1. A composition comprising a lubricating oil containing oxidation inhibiting amounts of dimorpholine monosulfide.

2. A composition comprising a lubricating oil containing about 0.10% to 2.0% of dimorpholine monosulfide, a compound having the structure:

3. A lubricant comprising a petroleum lubricating oil containing corrosion and oxidation inhibiting amount of dimorpholine monosulfide, a compound having the structure:

4. A lubricant comprising a petroleum lubricating oil containing about 0.10% to 2.0% of dimorpholine monosulfide, a compound having the structure:

C Ha-CH: CHz-C H:

5 O\ /NS-N CHr-CH: CHr-C H2 5. A lubricant comprising a. petroleum lubricating oil containing about 0.5% of dimorpholine monosulde, a compound having the structure: v GHr-CH:

ALFRED L. BAYES. 

